(6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Base Information

• Chemical Name: (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one
• CAS No.: 1218989-18-4
• Molecular Formula: C₂₁H₁₉NO₃
• Molecular Weight: 333.387

Synonyms:(6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Chemical Property of (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

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Technology Process of (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

There total 6 articles about (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

propargyl bromide (106-96-7) + (2S,4R)-ethyl 4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate (1041199-38-5) → (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (1218989-18-4)

Guidance literature:

(2S,4R)-ethyl 4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

propargyl bromide; In N,N-dimethyl-formamide; toluene; mineral oil; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2017.10.016

Reference yield: 52.0%

(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester (344791-02-2) + propargyl bromide (106-96-7) → (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (1218989-18-4)

Guidance literature:

(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester; With sodium hydride; In N,N-dimethyl-formamide; at -25 ℃; for 0.333333h; Inert atmosphere;

propargyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b03156

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (1218989-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 0 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / -25 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.6b03156

upstream raw materials:

propargyl bromide

(2S,4R)-ethyl 4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate

(2S,4R)-1-ethyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester

Downstream raw materials:

((2S,4R)-diphenyl-4-(prop-2-yn-1-yloxy)pyrrolidin-2-yl)methanol

(2S,4R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-4-(prop-2-yn-1-yloxy)pyrrolidine

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